Simarillion when I was in middle school. Not a good place to start; it set me back a full two decades on Tolkien. Read the trilogy when I was raising babies, Unfinished Tales shortly thereafter. Amazingly did not actually read The Hobbit until after those. So I went completely backwards.

Favorite Tolkien character:

Eowyn. She finally learns that when you can't be with the one you love, love the one you're with.